Photochemical, thermal, biological and long-term degradation of celecoxib in river water. Degradation products and adsorption to sediment

Abstract

Celecoxib is an anti-inflammatory drug with antibacterial activity whose fate in surface water is unknown. Thus, some assays have been conducted under forced biological, photochemical and thermal conditions, and non-forced conditions, to establish its persistence and degradation products in river water. The results suggest that celecoxib dissolved in river water is not biologically degraded while it is minimally altered after its exposure to sunlight or high temperature (70°C). Only the irradiation at 254nm promotes its complete degradation. Celecoxib is degraded about 3%, in 36 weeks, when water was kept at room temperature and the exposure to sunlight was partially limited as it happens inside a body of water. Residues were monitored by ultra-pressure liquid chromatography/quadrupole time-of-flight/mass spectrometry after solid-phase extraction; eleven degradation products were detected and the structures of nine of them were unequivocally proposed from the molecular formulae and fragmentation observed in high-resolution tandem mass spectra. The long-term transformation products under non-forced conditions were 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonic acid, 4-[1-(4-sulfoaminephenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]benzoic acid and a hydroxylated derivative. The degradation over time in presence of sediment was monitored, being slightly higher, about 4%. The adsorption equilibrium constants of celecoxib and degradation products on river sediment were estimated.